Ch.

23
Functional Groups
Functional Group
• An atom, group of atoms or type of bond in an organic
molecule that react in a predictable manner
• Symbol “R” is used to represent the hydrocarbon
fragment of the organic molecule
Alkyl Halides
• R-X
• Organic compounds containing halogens
• X = F, Cl, I or Br
• Prefixes are: F=fluoro, Cl= chloro, Br= bromo, I=iodo
• Halocarbons in which a halogen is attached to a
carbon of an arene ring are called aryl halides.
Naming Alkyl Halides

1. Name Parent Chain

1. Name Parent Chain

1-chlorobenzene
Alcohols
• R- OH
• Organic compounds
containing a
hydroxyl (-OH) group
Naming Alcohols
1. The parent chain must contain the atom attached to
the –OH group.
2. The parent chain ends with “-ol” instead of “-e”
3. Number the carbon atoms in the parent chain so
that the –OH group is given the lowest number
4. Name and identify positions of the branches
5. Name the compound
1-Ethanol 3-methyl-1-butanol

2-propanol
Alcohols
• Alcohols can have more than one hydroxyl group.
Alcohols
• Primary Alcohols: hydroxyl group is attached to an end carbon
CH3 - CH2 - CH2 - OH Propanol

• Secondary Alcohol: Hydroxyl group is attached to a carbon atom that is attached to 2 other
carbons
CH 3 -CH- CH3 2-Propanol

OH
• Tertiary alcohol: hydroxyl is attached to a carbon that is attached to 3 other carbons

CH3

CH3 -CH- CH3 2- methyl - 2-Propanol

OH
Fermentation
• Fermentation is the production of ethanol from sugars by the action
of yeast or bacteria. A second reaction product, carbon dioxide,
causes bread to rise
Reactions with Alcohols
• Addition reactions of alkenes are an important method of introducing new
functional groups into organic molecules.
• In an addition reaction, a substance is added at the double or triple bond of an
alkene or alkyne.
• Double and triple bonds between carbon atoms are much more reactive than
single bonds between carbon atoms.
• The addition of water to an alkene is a hydration reaction.
Ethers
• R—O—R
• An ether is a compound in which oxygen is bonded to two carbon
groups
• Ether oxygens are NOT generally part of the main chain in linear
ethers.
Naming Ethers (Common)
• The alkyl groups attached to the ether linkage are named in
alphabetical order and are followed by the word ether.
IUPAC Naming Ethers
• The larger of the two alkyl groups attached to the oxygen is considered to
be the parent compound
• The smaller alkyl group and the oxygen atom are considered to be a
substituent group on the parent compound with –oxy suffix
• Cyclic ethers are named as oxacycloalkanes with the oxygen being at
position 1 of the chain.
Carbonyl Groups
• A functional group with the general structure C═O.
• The C═O functional group is present in aldehydes and ketones.
Aldehydes
• An aldehyde is an organic compound containing an oxygen at the END of a parent
chain and double bonded to a carbon that is attached to at least one hydrogen.
• Naming Aldehydes:
1. The longest continuous chain containing the aldehyde group is considered
to be the parent compound.
2. The carbonyl carbon is part of the parent chain and is always considered to
be in the #1 position.
3. The suffix “al” is added to the name of the parent compound to indicate
that the compound is an aldehyde.
Naming Aldehydes

1-ethanal 2-chloro-1-pentanal
Ketone
• A ketone is an organic compound in which the carbon of the carbonyl group is joined to two other
carbons (found in the middle of a parent chain).

• Naming Ketones:
1. The longest continuous chain containing the ketone group is considered to be the parent
compound.

2. A number is included before the name of the parent compound to indicate the position of
the ketone group. The chain is always numbered so that the carbonyl carbon has the lowest
possible number.

3. The suffix “one” is added to the name of the parent compound to indicate that the
compound is a ketone.
Naming Ketones

3-methyl-2-butanone

2-pentanone

2,3-hexandione
Properties of Aldehydes and ketones
• Many aldehydes and ketones have distinctive odors.
• Aromatic aldehydes are often used as flavoring agents.
• Benzaldehyde is known as oil of bitter almond.
• Cinnamaldehyde is the source of the odor of oil of
cinnamon.
Carboxyl Groups
• Carboxyl groups consist of a carbonyl group (C═O) attached to a
hydroxyl group (-OH)
Carboxylic Acids
• A carboxylic acid is a compound with a
carboxyl group
• The general formula for a carboxylic acid is
RCOOH
• Contains a carbonyl (C=O) and a hydroxyl (-OH)
• Carboxylic acids give a variety of foods a
distinctive sour taste
Naming Carboxylic Acids
1. The longest continuous chain containing the carboxyl group is
considered to be the parent compound.
2. The carboxyl carbon is part of the parent chain and is always
considered to be in the #1 position.
3. The suffix “oic” is added to the name of the parent compound, and
the word “acid” is added to the name.
Properties of Carboxylic Acids
• Pungent odors, but odor decreases as number of C-atoms increases
• Carboxyl group is often found in fatty acids, that are natural occurring
in fats and oils
Ethanoic Acid – Acetic Acid – Vinegar
Methanoic Acid- Formic Acid – Irritant found in the ant and bee stings
Octadecanoic Acid – Stearic Acid – fatty acid found in animal fats used in making soaps & candles
Butanoic Acid – Butyric Acid – found in butter, used in plastic manufacturing
Ethanedioic Acid – Oxalic Acid – found in plants, used in wood bleaching
Esters
• Esters contain a carbonyl group and an ether link to the carbonyl
carbon
• General formula for a ester is RCOOR
• Derivatives of carboxylic acids in which the –OH of the carboxyl group
has been replaced by an –OR from an alcohol
Naming Esters
1. Determine the name of the “R” group (alcohol).
2. Place the name of the “R” group in front of the name of the parent
acid, forming two words. Change the ending to -yl
3. Determine the name of the parent acid, and change its suffix from
“—ic” to “—ate.” Drop the word “acid.”
Preparation of Esters
• Esters may be prepared from a carboxylic acid and an alcohol.
Properties of Esters
• Many are used in
artificial flavorings,
fragrances, and
perfumes
• Many esters smell
fruity
• Many are volatile
Amine
• Organic compounds related to ammonia (NH3)
• Three kinds:
• Primary – one hydrogen in ammonia has been replaced
with a alkyl group
• Secondary - two hydrogen atoms in ammonia have been
replaced by two alkyl groups
• Tertiary – all three hydrogen atoms in ammonia have been
replaced by three alkyl groups
Amines
• Primary amines are named by treating the –NH2(amino) group as a
substituent group on the longest (parent) chain
• Number the chain so you have the lowest values
• Indicate the number the amino group is on
 Amines
• Secondary and tertiary amines are named according
to a “common” naming system
• When naming secondary and tertiary amines, name
the branches off of the nitrogen in alphabetical
order. Use prefixes if more than one of the same
branch.
Amides
• A carboxyl group that has -NH2 replacing the -OH
Amides
• Naming Amides
• Identify the carboxylic acid from which the amide was derived and change the
suffix from “-oic” to “amide” and drop the word acid
• Add the names of any branch chains